quinolinedithiol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: quinolinedithiol
• 英文别名: Dimercaptoquinoline；3-sulfanyl-1H-quinoline-2-thione
• 化学式: C₉H₇NS₂
• 分子量: 193.293
• InChiKey: HSZANWKPRRXMFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  quinolinedithiol 在 盐酸 、 sodium hypochlorite 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-chloro-3-chlorosulfonylquinoline
  参考文献：
  名称：

  From 2,3-, 2,6-, 3,4- and 4,6-Dichloroquinolines to Isomeric Chloroquinolinesulfonyl Chlorides

  摘要：

  The action of sodium methanethiolate (in boiling DMF) on x,y-dichloroquinolines (1) (x=3 or 6, y=2 or 4) occured via chlorine ipso-substitution followed by methanethiolato-S-demthylation to yield x,y-quinolinedithiolates 2A which were: i) subjected to S-methylation, ii) oxidatively chlorinated to y,y'-bis(x-chloro-x-quinolinesulfonyl chlorides (5). Oxidative chlorination of y,y'-bis(x-chloro quinolinyl) disulfides (7) led to x-chloro-y-quinolinesulfonyl chlorides (8) accompanied by x,y-dichloroquinolines (1). Both quinolinessulfonyl chlorides 5 and 8 were efficiently converted to the corresponding quinolinesulfonamides 6 and 9.

  DOI：

  10.3987/com-09-11855
• 作为产物：
  描述：

  2,3-二氯喹啉 、 sodium thiomethoxide 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 4.0h， 生成 二甲基硫 、 quinolinedithiol
  参考文献：
  名称：

  From 2,3-, 2,6-, 3,4- and 4,6-Dichloroquinolines to Isomeric Chloroquinolinesulfonyl Chlorides

  摘要：

  The action of sodium methanethiolate (in boiling DMF) on x,y-dichloroquinolines (1) (x=3 or 6, y=2 or 4) occured via chlorine ipso-substitution followed by methanethiolato-S-demthylation to yield x,y-quinolinedithiolates 2A which were: i) subjected to S-methylation, ii) oxidatively chlorinated to y,y'-bis(x-chloro-x-quinolinesulfonyl chlorides (5). Oxidative chlorination of y,y'-bis(x-chloro quinolinyl) disulfides (7) led to x-chloro-y-quinolinesulfonyl chlorides (8) accompanied by x,y-dichloroquinolines (1). Both quinolinessulfonyl chlorides 5 and 8 were efficiently converted to the corresponding quinolinesulfonamides 6 and 9.

  DOI：

  10.3987/com-09-11855

文献信息

• From 2,3-, 2,6-, 3,4- and 4,6-Dichloroquinolines to Isomeric Chloroquinolinesulfonyl Chlorides
  作者：Krzysztof Marciniec、Andrzej Maślankiewicz

  DOI：10.3987/com-09-11855

  日期：——

  The action of sodium methanethiolate (in boiling DMF) on x,y-dichloroquinolines (1) (x=3 or 6, y=2 or 4) occured via chlorine ipso-substitution followed by methanethiolato-S-demthylation to yield x,y-quinolinedithiolates 2A which were: i) subjected to S-methylation, ii) oxidatively chlorinated to y,y'-bis(x-chloro-x-quinolinesulfonyl chlorides (5). Oxidative chlorination of y,y'-bis(x-chloro quinolinyl) disulfides (7) led to x-chloro-y-quinolinesulfonyl chlorides (8) accompanied by x,y-dichloroquinolines (1). Both quinolinessulfonyl chlorides 5 and 8 were efficiently converted to the corresponding quinolinesulfonamides 6 and 9.